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I have some very old Pi 3Bs installed in the field that are running Raspbian Jessie and openssl version 1.0.1t. I believe Buster was the first to include TLS 1.3 and doing an upgrade from Jessie to Buster on a system I do not have physical access to gives me heartburn. The Pi needs to talk to a Pepwave MAX ethernet modem, which recently removed support for TLS 1.2 from its web UI, even for local connections. Its using python 3.4 and the requests (2.23.0) library to communicate with the modem.

Is getting TLS 1.3 on these systems even feasible? I have looked into building openssl from source but I am guessing I would also need to re-build python to include the newer openssl version... I was hoping to get some feedback on whether this is even going to be possible or if I am out of luck.

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    SSL isn't built into the python interpreter itself, it's linked to a .so file that's effectively part of the module. That said, the source for that appears to be part of the cython core, and I don't know how feasible just compiling that object will be without the rest -- if it is, this should be pretty quick and easy, but you will need a version of openSSL w/ TLS1.3 available.
    – goldilocks
    Dec 16, 2023 at 20:01

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